


Shinichi and Dresses

by ReindeerGamesofMischief



Category: Magic Kaito, 名探偵コナン | Detective Conan | Case Closed
Genre: Crossdressing Kink, Embarrassed Shinichi, M/M, Possessive Kaito, Sex Proposal, kaishin - Freeform
Language: English
Status: Completed
Published: 2015-10-14
Updated: 2015-10-14
Packaged: 2018-04-26 07:25:16
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,737
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4995535
Author URL: https://archiveofourown.org/users/ReindeerGamesofMischief/pseuds/ReindeerGamesofMischief
Summary: <blockquote class="userstuff">
              <p>What starts with one dress, ends up being a second and a third.</p>
            </blockquote>





	Shinichi and Dresses

**Author's Note:**

> Hey everyone! So I got back into Meitantei Conan and dear lord this fandom is beautiful and all things wonderful. Especially KaiShin. Yesssss.
> 
> But I digress! I saw a picture of Shinichi in a wedding dress and Kaito in a tux and just….this came to be. Sorry for any OOCness.

Shinichi stared at himself through the mirror. Well, it wasn’t _himself_ he was really looking at, but the outfit that Kaito had put on him. Over the last few years, he’s grown accustom to Kaito’s tricks and quick hands. Shinichi has already lost count the amount of times his thief has changed his outfit without him realizing. 

“Don’t you like it Shin-chan?”

Blue eyes flickered over to the reflection of the smiling magician. Kaito was standing behind him with that happy smile of his, looking innocent. The detective just knew behind that innocent smile lay the devious thoughts of a master pervert.

“You don’t expect me to leave for work like this, do you?”

Kaito blanched. “Like hell I want anyone seeing you dressed like this.”

A second later, Shinichi was wrapped in Kaito’s arms as the thief tips his chin up to stare into his eyes. “This is for my eyes only. I’m almost jealous that _you_ get to see this.”

“B-Barou!” blushed Shinichi as he looked away again. This time in embarrassment. Back in the early stages of their relationship when Kaito spoke so familiarly, Shinichi would push or smack the older teen. Kaito had no shame, and still didn’t have any. However, Shinichi has learnt to deal with his perverted partner’s statements and requests. At least sort of.

That’s why when Shinichi felt the sudden grope on his backside he only yelped and tucked his head into Kaito’s neck. If he tried to squirm out of Kaito’s arms the thief would just get more enthusiastic about it.

Kaito hummed happily. Shin-chan didn’t push him away or demand that his clothes be returned. His smile turned into a perverted leer as he looked at his tantei-kun’s body decked out in all white. When Kaito saw the design online while perusing for new costumes for his magic shows, he happened across a fantasy costume website. It was a simple website that allowed amateur designers sell their own costumes. Most shops looked like cheap knock-offs or slutty imitations of already great designs. 

Whether he was Kaito or Kaitō KID, nothing but the best would do. Imagine to his surprise that right before he closed the website he came across a shop that sold a variety of wedding dresses. And while he knew his Shin-chan was against cross-dressing, the fantasy of seeing his Shin-chan in a dress with his adorable blush was too good to pass up. 

Three clicks and a few buttons later, he purchased a Lolita-styled wedding dress and began planning on how to get his Shin-chan in it. And what a success it was!

The knee length dress fit perfectly. It had a full tulle skirt with capped lace sleeves. The bust area didn’t look ridiculous either with Shinichi’s flat chest. But that wasn’t his favorite part of the dress. No. It was the endless amount of legs that were available to his eyes. 

He’s not ashamed to admit that he was an ass and leg kind of guy. His shin-chan had a glorious ass (unfortunately covered), and delectable legs (bare to his eyes) and the detective was very aware of Kaito’s obsession. 

“Kai-chan,” pleaded Shinichi, easily gaining the taller man’s attention with the nickname. “I need to go to work.”

Kaito sighed, but snapped his fingers instantly putting Shinichi back into his preferred work outfit of black slacks, black dress shirt, and charcoal suit jacket. Though Shinichi was mostly covered, the pants did show off his butt better. 

“We’ll pick this up when you get back,” promised Kaito leaning down to steal a kiss.

Shinichi hummed in agreement as he returned the kiss. The dress had been embarrassing, but…lately he’s liked it when Kaito puts him in dresses. He hasn’t admitted it out loud yet, but if the thief kept it up he might not have to reveal it. Kaito would just _know_.

\--KaiShin--

A month after Kaito putting him in a Lolita wedding dress, Shinichi found himself at a bridal boutique with Sonoko, Ran, Aoko, and Kazuha. The bride-to-be was Sonoko. A couple weeks ago Makoto had finally popped the question and the blonde heiress had been so overjoyed.

Now however…

“Are you _sure_ there isn’t a dress here that can fit all these requirements?” asked Ran, well more like begged. 

Shinichi rolled his eyes. How on earth did he get dragged into this? Kaito was out, surveying his next legal performance location when the four of them dropped by their apartment. Next thing he knew, four girls giggling and chatting about weddings and dresses surrounded him. 

He could’ve sworn he had left this life behind when he stopped being Conan. None of them knew of his stint as Conan, but he noticed that every once in a while he would be treated like when he was Conan. Ran had gone from a love interest to an older sister.

An older sister who dragged him out on all-girl outings completely disregarding that he was very much male thank you very much.

“How about this dress?”

Shinichi grimaced at the atrocity, quickly walking away between the aisles of dresses.

“Shinichi-kun?” questioned Aoko, the only one who caught him sneaking off.

“I’m just going to look around, okay?”

She laughed nodding and waved him off. Kazuha and Ran were now asking about the bridesmaid dresses.

Finally partially relieved, he looked around. The bridal shop was on the high-end side of things. Sonoko was like Kaito in that she wanted nothing but the best. Which Shinichi could respect…up to a certain point.

He saw another dress filled with frills and like a cotton candy machine threw up on a dress. Why would someone design something so terrible?

None of these dresses were eye catching in a positive way. 

“Excuse me sir? Do you need any help?” asked one of the attendants. The man was a little older than him, but had a very charming smile. 

“Uh no. I’m here with a friend, and to be honest I’m just hiding.”

The attendant chuckled. “You are not the first. Friend of the groom or bride?”

“The bride,” he responded. It was then when he actually spotted a dress that he wanted to try on. “Excuse me…that dress…could I…um…”

Looking over his shoulder, the attendant saw the dress that Shinichi was pointing at while blushing. It was a floor length dress with a high waist and no sleeves. It was an elegant and classic style dress. “An excellent choice sir. How about I get your measurements so we can get you the right fit?”

Shinichi blushed nodding. “You’re not-“

“Freaked out?”

“Well that wasn’t the wording I would use, but yeah.”

Laughing the attendant grabbed the measuring tape around his neck. “Believe it or not, I’ve done this several times already. Lift your arms please.”

Later that evening when Shinichi finally made it home, Sonoko finding a dress and the girls happy with their bridesmaid dresses, the detective was shoved against the apartment door with Kaito kissing the life out of him.

“Dammit tantei-kun,” murmured Kaito, hands sliding down Shinchi’s hips and back to grope the detective’s ass. “You had to send me a picture.”

Shinichi’s blush darkened. He hadn’t sent a picture, but his money was on Aoko since she was the one who found him later.

\--KaiShin--

The third dress, hadn’t been a wedding dress, but made Kaito jealous. Gloved hands, his favorite blush, and pleading sapphire eyes stopped him from exploding on the police department for their latest trap.

Like always during Kaitō KID heists, Nakamori-keibu was shouting at his unit while they diligently pinched cheeks. The jewel was enclosed in its display case waiting to see what happens. 

The only difference was that it wasn’t Kaitō KID who was stealing the gem. Since Kaito had no plans to steal any gem…that week, _he_ knew the notice that was sent in was a fake. 

His task force on the other hand was treating it like a real KID heist. 

“Ne, Occhan?” questioned Kaito, interrupting Nakamori-keibu.

“O-Oh. Kaito, you’re here today?” The keibu was slightly startled, but Kaito wasn’t an unexpected guest since Shinichi was at every KID heist and sometimes the magician would tag along. After all, while Kaito was a total KID fan, he didn’t share his detective boyfriend with anyone, even KID who had a very strong interest in the Kudo-gaki.

“I’m actually here to pick-up Shin-chan, but I can’t find him.” 

“H-He’s uhhh…changing. We finally have s-something that will finally stop that menace!”

Before Kaito could question the keibu about his sudden penchant for stuttering, behind them came Shinichi’s voice suddenly. “ _And I told you Nakamori-keibu_ , this isn’t a KID heist.”

Kaito spun around smile on his face, raising an eyebrow at the overcoat that Shinichi wore. How was this supposed to catch his attention? Honestly, all the detective had to do was smile at him…or frown…or glare. Shinichi could do nothing and Kaito’s attention would be caught. However, unless Shinichi’s life was in danger, the magician wouldn’t stop his heist.

“K-Kaito!” stuttered Shinichi, his blush growing as he huddled further under his overcoat. “W-What are you doing here?”

“Came to pick you up…are you wearing heels?” Violet eyes widened the longer they took in Shinichi’s lovely feet incased in heels. The thief could see quite a bit of leg before the over coat got in the way. What in the world was going on?

“Kai-

“IT’S TIME!”

The lights shut off, drenching everyone in darkness. Kaito was easily able to adjust to the light change thanks to his own heists. What he wasn’t able to adjust to was when the light turned on and saw what exactly his Shin-chan, _his tantei-kun_ , was forced to wear by Division Two.

Thigh-length white dress with light blue accents that would match KID’s shirt, the corset that tied in the front was done with red ribbon. The skirt was a soft mix of light blue and white tulle and left a train in the back. A monocle sat on Shinichi’s blushing face with a little top hat that was pinned to his head and had a bow of tulle attached to it in pure blue like the ribbon on his KID top hat. Shinichi wore quarter length gloves and booted heels with garters peaking out from under the skirt.

“W-what?”

Shinichi blushed, biting his lip. He hadn’t planned on his boyfriend seeing him like this. “Kaito? Hey? Kaito!” When that didn’t get an answer, Shinichi used his secret weapon. “Kai-chan!”

Kaito snapped out of his daze, grabbing Shinichi to him to hide as much as he could. The longest thing that he had on him that would cover Shinichi was his cape from his KID costume. And Nakamori had flung Shinichi’s over coat too far for him to retrieve without letting more people get a glimpse of Shin-chan.

“The hell is this Occhan?! You can’t _pimp out_ my boyfriend!” Kaito than turned to Shinichi about to yell at him for letting them get him in such a getup for the public to see. But two gloved hands caught his face as sapphire eyes bore into his own indigo set. “Don’t try-“

“Kai-chan,” blushed Shinichi. Both were in their own little world as the police task force chased after the fake KID. “Don’t get mad.”

Kaito didn’t get mad. Oh no…he got even. He also **borrowed** the dress later for Shin-chan to wear at home for his eyes only. After all, his tantei-kun made a very lovely Mrs. KID.

\--KaiShin--

Shinichi and Kaito have finally reached the point in their relationship where they shared not only trust and love, but also all of their secrets. It was no longer a rare occasion that Shinichi was in a dress while they were just at home and not expecting guests. Of course many of their friends caught him in a dress, but they understood.

Shinichi also would bet money that they all think it was Kaito’s fault he was in a dress, and none of them bothered to question Kaito on his fetishes and fantasies. For a friendly and polite magician, Kaito also had a _very_ mean aspect to his personality as Division Two got to learn after the Mrs. KID costume. 

Looking over at his contemplative boyfriend, Shinichi decided it was time to confront the magician. Stepping out on the patio, the warm afternoon breeze brushed by.

“Kaito?” questioned Shinichi softly as he slipped on to Kaito’s lap. Talented hands wrapped around his waist securely.

“Hm?”

“Isn’t it about time?”

Kaito blinked out of his trance to look up at mischievous indigo eyes. “Time? For what Tantei-kun.”

Shinichi leaned in, the short dress that he was wearing rode up, exposing more and more leg to the suddenly interested indigo gaze that were locked on them. Wrapping his arms around the thief’s neck, he whispered into Kaito’s ear. “To finally make me yours? To make me say ‘I do’?”

Kaito stiffened for all of two seconds before he had them on their bed. Deft hands had his erection free from their confines, and Shinichi’s dress pushed up exposing the panties beneath. Not just any panties though. Oh no. These were silk and crotchless. Shinichi’s erection stood erect and beautiful.

“ _Kai_ ,” begged the detective wiggling around and exposing more of his stomach. Kaito knew that Shinichi was already prepped for him. There was no way his Tantei-kun would go to such efforts of seducing him (not that it took much!) and not prep himself before hand. While disappointed that Kaito missed what would’ve been without a doubt breathtakingly arousing to watch, Kaito did as Shinichi pleaded. Well…sort of.

Grabbing his arousal, he lined himself up with Shinichi’s pink hole. And instead of thrusting right in, Kaito pushed in far enough so _barely_ the head was in. Oh the thief knew it would drive Shinichi _crazy_. 

“ _Kaito!_ ” squirmed Shinichi wanting more. Kami-sama did he need to be _filled_. He needs to feel full! Full of Kaito! And the damn thief wouldn’t budge! Not a single millimeter. Kaito’s grip on his hips stopped even the detective from moving closer. “ _More!_ ”

“You’re such a cum-slut,” chuckled Kaito, well aware what Shinichi was demanding from him. But not just yet, he still had one thing to do. Quickly, but gently he grabbed Shinichi’s left hand raised it to his lips.

“Marry me.”

Shinichi hissed when Kaito gave a shallow thrust before pulling out a little further than he was previously. It wasn’t fair, pouted Shinichi. His stupid thief had such solid control that he could drive Shinichi crazy for _hours_ if he wanted to. And if Shinichi knew any better, if he didn’t say ‘yes’, that’s exactly what Kaito would do. Torture him to the brink of almost breaking him without ever giving him what he wants. 

“Y-You never do things normally, do you?

“Were you expecting less?” Kaito did that small thrust in before almost completely pulling out again.

“Of course not. That would’ve been idiotic.”

“Yup,” agreed Kaito thrusting in, before pulling almost out patiently waiting for his answer.

“Dear Kami-sama! Yes Kaito, I’ll marry you!”

Smirking, Kaito kissed Shinichi’s ring finger where already there was a white gold band with a modest diamond snuggled between two sapphires. “Good, because I already found you the dress.”

“Ka- _ITO!_ ” screamed Shinichi as Kaito finally, _finally_ thrusted all the way in and set into a rough speed.

After various rounds of lovemaking, Shinichi finally sighed in contentment as he sat propped against Kaito’s chest who was leaning against their headboard, completely relaxed. One of Shinichi’s hands rested on his lower stomach that was sore and distended with every drop of cum that Kaito released these last couple of hours.  
And since Shinichi was greedy about Kaito’s cum, the thief was no longer surprised when he was asked to plug him up. It was habit now to plug Shinichi after sex. If Kaito was honest with himself, he enjoyed seeing Shinichi likes this too. Good thing Kaito never lied to himself about these things!

Kaito caught Shinichi looking at his engagement ring. “Are you happy?”

“Aa,” agreed the dazed detective, softly moaning as the plug rubbed against prostate as he shifted closer to Kaito. “You?”

“Like I could be anything else less when I’m with you.”

Blushing, Shinichi lightly smacked Kaito’s thigh. “Corny!”

**Author's Note:**

> Hope you liked it!


End file.
